Vacation rentals in Monsigliolo

Tuscan charm of villa - countryside - Villa Senaia

In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas

Location · Value · Comfort

Casa I Pini

Casa I Pini has spacious and comfortable interiors. The main building, the Leopoldina, has two entrances on the ground floor. The first access takes you directly to the spacious kitchen, equipped with everything needed for cooking and complete with dining table; the kitchens location is very convenient in order to reach the gazebo and the outdoor barbecue. On the left side of the kitchen there is a small living room with sofa, satellite TV and DVD; on the right side instead you will access ...

Location · Family · Nearby

Rural Tuscany | Family farmstay with restaurant

Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

Value · Location · Pets

Stunning Tuscan Villa & Panoramic Infinity Pool

Stunning Tuscan hilltop Villa, with infinity edge swimming pool, has sweeping 180° panoramic views to Cortona, Lake Trasimeno and the entire Val Di Chiana. The perfect family retreat within ancient sun-drenched olive groves. 5 Double bedrooms; 4 bathrooms; new fully integrated kitchen & dining living space; living room with fireplace; TV snug; stone BBQ & outdoor kitchen within dining terraces and gardens; covered breakfast porch; parking; private infinity pool with sunset views.

Family · Location · Access

[Antico Casale]Tuscan Views & Private Pool Cortona

Entire farmhouse finely restored to bring back the authentic spirit of a historic stone farmhouse in Cortona. ✔ Suitable for up to 12 guests ✔ Private swimming pool ✔ 1 km from the center of Cortona ✔ Property composed of the main farmhouse on two levels (ground floor and first floor) plus a separate dependance ✔ 3 double bedrooms, 2 twin bedrooms, 1 sofa bed ✔ 3 fully equipped kitchens, 3 full bathrooms, private parking ✔ Outdoor space with a unique view and dining tables

Location · Family · Air conditioning

Villa with Private Pool in the Tuscan Countryside

Modern villa with private pool, waterfall, large garden and relaxation area. Divided into: Suite with hydromassage bathtub, private bathroom and small refreshment corner; Apartment with 2 bedrooms, equipped kitchen and a second bathroom in elegant white faux marble. Perfect for families and groups up to 7. Features American BBQ, panoramic gazebo, ping pong, outdoor dining area and poolside shower. Close to Cortona, Arezzo, Montepulciano, Siena and the Crete Senesi.

Family · Location · Hospitality

Il Giardino degli Ulivi | Casa Ippocastano

Il Giardino degli Ulivi is a farmhouse in the heart of Tuscany, surrounded by olive groves and only 3 km away from the charming town of Cortona. The property features 6 restored farmhouse apartments, each offering authentic Tuscan character, modern comforts, and private outdoor spaces. Guests can enjoy peaceful garden, scenic views, and relax by the swimming pool, as well as easy access to Tuscany’s rich history and vibrant cultural offerings.

Value · Family · Walkability

Villa Bellora | Pool & Panoramic Views | Cortona

Villa Bellora: Your Tuscan Summer Escape Perched among Tuscany's rolling hills and vineyards, Villa Bellora sits 20 minutes from both Cortona and Montepulciano. Spend your days by the private pool, with a sun deck overlooking the views. Three bedrooms, two bathrooms — ideal for families, couples, or friends. Tuscany's best wine estates, hilltowns, and thermal spas are all within reach. We're happy to share our favorite local spots.

Location · Family · Comfort

Villa Pergo is an ancient charming country villa

Stay in a piece of Tuscan history at Villa Pergo, a charming countryside estate dating back to 1640. Surrounded by olive groves and rolling hills near Cortona, the villa offers authentic character, panoramic views, and a beautiful infinity pool. With space for up to 11+1 guests in 6 bedrooms, large gardens and peaceful surroundings, it is the perfect retreat for families or groups looking to experience the true charm of Tuscany.

Family · Location · Sleep quality

Casa del Passerino

Apartment located inside a historic building in Cortona, dating back to the 1500s, overlooking the city's main square... Our property, while condemning the war, dissociates itself from all racist behavior towards the Russian and Belarusian population. At Casa del Passerino, people of these nationalities are welcome and will be treated the same as everyone else. We look forward to seeing you in Tuscany!

Family · Location · Comfort

Cortona Shabby Chic House - independent & balcony-

This is an apartment cared for by a Superhost who lives in Cortona every day. My place is located in the heart of the historic center just a few steps from the main squares and streets This cute apartment is recently renovated and sleeps up to 3 people. Independent apartment with single entrance all on one floor, with balcony. Thoughtfully furnished, equipped with all the comforts for total relaxation

Family · Value · Layout

18th-century farmhouse in Cortona, garden, and 4 bathrooms

5 minutes from Cortona, a tastefully restored 18th-century stone farmhouse: frescoes, beams, and original terracotta, surrounded by sunflowers and cypresses. Private garden and great silence, with all the modern comforts. Up to 7 guests, 4 bathrooms, air conditioning in every room, and utilities always included. The ideal base for experiencing Tuscany at a leisurely pace, in total privacy.

Location · Family · Cleanliness